Edward Furlong & Natasha Lyonne
Edward Furlong — forever John Connor to Terminator 2 fans — dated Natasha Lyonne in the late ’90s after meeting on the set of Detroit Rock City. They were both rising stars with a bit of an edge, and while the romance didn’t last, it was peak alternative-’90s energy. Natasha has gone on to huge success with Russian Doll and Poker Face, and Edward… well, let’s just say his post-’90s journey has been a lot more complicated.
Scott Speedman & Keri Russell
Fans of Felicity will remember Scott Speedman and Keri Russell’s on-screen romance as Ben and Felicity — but they also dated in real life. It was the perfect mix of life imitating art, though it didn’t last forever. They’ve both moved on romantically but have stayed good friends. Scott’s a dad now, and Keri’s in a long-term relationship with Matthew Rhys (and yes, they’re as cute together as you’d imagine).
Kathy Griffin & Jack Black
Yes, this actually happened. Comedian Kathy Griffin and Jack Black went out a couple of times in the ’90s, and she still teases him about it — especially the time she discovered his “shower towel” was actually his bath mat. It wasn’t a big love story, but it’s a great anecdote. Now Jack’s happily married with kids, and Kathy’s still delivering unfiltered, hilarious commentary on everything.
Andrew Keegan & LeAnn Rimes
Andrew Keegan and LeAnn Rimes’ relationship started like a teen movie — literally. LeAnn spotted him in a magazine when she was 15, said he was cute, and her manager called him. They dated for about three years, which is basically a lifetime in teen romance years. Now LeAnn’s married to Eddie Cibrian and is a stepmom to his two sons, and Andrew is a dad to daughter Aiya Rose.
